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860667P

Avanti

4E,8Z-Sphingadiene

Avanti Research™ - A Croda Brand 860667P, powder

Synonym(s):

(2S,3R,4E,8Z)-2-aminooctadec-4,8-diene-1,3-diol

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About This Item

Empirical Formula (Hill Notation):
C18H35NO2
CAS Number:
41679-33-8
Molecular Weight:
297.48
MDL number:
MFCD32697033
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 1 mg (860667P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860667P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@@](N)([H])[C@]([H])(O)/C=C/CC/C=C\CCCCCCCCC

InChI

1S/C18H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h10-11,14-15,17-18,20-21H,2-9,12-13,16,19H2,1H3/b11-10-,15-14+/t17-,18+/m0/s1

InChI key

RTQVJTLVVBJRJG-NZDSQIAKSA-N

General description

4E,8Z-Sphingadiene is a unique sphingoid base containing C18 chain, with trans double bond at C-4 and cis double bond at C8. It is widely present in plant tissues, but very minimal in mammals.

Application

4E,8Z-Sphingadiene has been used as an standard in liquid chromatography with tandem mass spectrometry (LC-MS-MS) method for quantitation of chemopreventive sphingadienes in food products and biological samples.

Biochem/physiol Actions

Sphingadienes are growth-inhibitory sphingoid bases, which play a vital role in apoptosis and cell signaling. Sphingadienes isolated from plants exhibit anti-inflammatory properties by inhibiting tumor necrosis factor α (TNF α) activity.

Packaging

5 mL Amber Glass Screw Cap Vial (860667P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

No data available

flash_point_c

No data available

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J H Suh et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1061-1062, 292-299 (2017-08-05)
Colorectal cancer (CRC) is a leading cause of cancer mortality. Diet has a significant influence on colon cancer risk. Identifying chemopreventive agents, dietary constituents, practices and/or diet supplements that promote gut health and reduce the incidence of intestinal neoplasias and
O Renkonen et al.
Journal of lipid research, 10(6), 687-693 (1969-11-01)
The dienic long-chain base (sphingadienine) of human plasma sphingomyelins has been identified as d-erythro-1,3-dihydroxy-2-amino-4-trans-14-cis-octadecadiene. A similar sphingosine was also detected in plasma sphingomyelins of rat, rabbit, and cat. The key reaction in the structural studies was partial reduction of sphingadienine
An LC/MS/MS method for quantitation of chemopreventive sphingadienes in food products and biological samples
Suh JH, et al.
Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 1061, 292-299 (2017)
Structure of plasma sphingadienine
Renkonen O and Hirvisalo EL
Journal of Lipid Research, 10(6), 687-693 (1969)
Rodell C Barrientos et al.
Journal of the American Society for Mass Spectrometry, 28(11), 2330-2343 (2017-08-24)
Glycosphingolipids are essential biomolecules widely distributed across biological kingdoms yet remain relatively underexplored owing to both compositional and structural complexity. While the glycan head group has been the subject of most studies, there is paucity of reports on the lipid
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